Ethanol → 3-Chloro-5-(hydroxymethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

(Step 1) To a mixed solution of methyl 3-(aminocarbonyl)-5-chlorobenzoate (2.2 g) in tetrahydrofuran:ethanol=10:1 (33 ml) was added lithium tetrahydroborate (0.34 g) at room temperature. After stirring at 60° C. for 2 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=5:1) to give 3-chloro-5-(hydroxymethyl)benzamide (0.95 g).

Provenance & Evidence